Sodium Bicarbonate → 4-(2-Chloro-4-aminobenzoyl)-5,6,7,8-tetrahydro-4H-thieno[3,2-b]azepine

HRID 2255960Notes

Reaction equation

[Cl:1][C:2]1[CH:19]=[C:18]([N+:20]([O-])=O)[CH:17]=[CH:16][C:3]=1[C:4]([N:6]1[CH2:12][CH2:11][CH2:10][CH2:9][C:8]2[S:13][CH:14]=[CH:15][C:7]1=2)=[O:5].C([O-])(O)=O.[Na+]>C(O)C>[Cl:1][C:2]1[CH:19]=[C:18]([NH2:20])[CH:17]=[CH:16][C:3]=1[C:4]([N:6]1[CH2:12][CH2:11][CH2:10][CH2:9][C:8]2[S:13][CH:14]=[CH:15][C:7]1=2)=[O:5]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 5.0 g of 4-(2-chloro-4-nitrobenzoyl)-5,6,7,8-tetrahydro-4H-thieno[3,2-b]azepine, 16.8 g of stannous chloride dihydrate in 184 ml of ethanol is heated at 80° C. under argon for 1 hour. The solution is cooled in an ice bath and made basic by the slow careful addition of 1M NaHCO3 (ca. 380 ml). The mixture is stirred for 1 hour at room temperature and extracted with 400 ml of ethyl acetate. The aqueous layer is extracted with an additional 250 ml of ethyl acetate. The extracts are combined and washed with 300 ml of brine, dried (Na2SO4) and filtered through a thin pad of hydrous magnesium silicate. The filtrate is concentrated under vacuum to give a white solid which is recrystallized from ethyl acetate to give 4.23 g of off-white crystals, m.p. 176°-179° C.

Workup

temperatureThe solution is cooled in an ice bath
extractionextracted with 400 ml of ethyl acetate
extractionThe aqueous layer is extracted with an additional 250 ml of ethyl acetate
washwashed with 300 ml of brine
dry with materialdried (Na2SO4)
filtrationfiltered through a thin pad of hydrous magnesium silicate
concentrationThe filtrate is concentrated under vacuum
customto give a white solid which
customis recrystallized from ethyl acetate

Sources & evidence

ORD record: ord-66f8a26a264c4279ac203c7fc05b0869
Source dataset: uspto-grants-1997_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05654297

Reaction notes

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